Methanol → HCID 118235802, compound

HRID 626994Notes

Reaction equation

HRID 626994 reaction equation
[F:1][CH:2]([F:29])[O:3][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[CH2:6][C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[CH:17]=[N:18][C:19](SC)=[N:20][CH:21]=3)[CH:14]=[CH:15][C:10]2=[N:9][C:8]=1[CH3:24].O[O:31][S:32]([O-:34])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].[CH3:44]O>CC(C)=O.O>[F:29][CH:2]([F:1])[O:3][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[CH2:6][C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[CH:21]=[N:20][C:19]([S:32]([CH3:44])(=[O:34])=[O:31])=[N:18][CH:17]=3)[CH:14]=[CH:15][C:10]2=[N:9][C:8]=1[CH3:24]

Participants

7

Reactant 4

HCID 887MethanolHCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfiteHCID 118235535HCID 118235535, compound

Product 1

HCID 118235802HCID 118235802, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution of Example 268 (4 g, 9.697 mmol) in MeOH (150 mL) and acetone (20 mL) at 0° C. was treated with Oxone® (potassium peroxymonosulfate; 11.92 g, 19.39 mmol) in water (100 mL). The resulting suspension was allowed to warm to r.t. and stirred for 18 h. The reaction mixture was treated with water and extracted with DCM (4×300 mL). The combined organic layers were concentrated in vacuo. A portion of the resulting crude yellow solid (4.4 g, 100%) was further purified by preparative HPLC to give the title compound (56 mg was obtained from 130 mg of crude material) as a white solid. HPLC-MS (pH 10): MH+ m/z 445.6 [M+H]+, RT 1.54 minutes.

Workup

  1. extractionextracted with DCM (4×300 mL)
  2. concentrationThe combined organic layers were concentrated in vacuo
  3. customA portion of the resulting crude yellow solid (4.4 g, 100%) was further purified by preparative HPLC

Sources & evidence

ORD record
ord-125f61291e0940d4968022b96ce34c79
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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